


The Wager

by shinysparks



Category: Sleepy Hollow (TV)
Genre: Crack, F/M, Fluff and Crack, Ichabod learns slang the hard way, No Revolutionary War soldiers were harmed in the making of this fic, or their cracks
Language: English
Status: Completed
Published: 2015-09-26
Updated: 2015-09-26
Packaged: 2018-04-23 10:06:01
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,459
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4872712
Author URL: https://archiveofourown.org/users/shinysparks/pseuds/shinysparks
Summary: <blockquote class="userstuff">
              <p>When Ichabod loses a bet with Abbie, he finds himself in a very uncomfortable predicament. ;)</p>
            </blockquote>





	The Wager

**Author's Note:**

  * For [Thymelady](https://archiveofourown.org/users/Thymelady/gifts).



> A gift for Thymelady, in hopes it might help things. KRYA PÅ DIG! <3
> 
> Also, this is my first work in this fandom and I haven't seen Sleepy Hollow in months (in fact, I've not seen all of season 1 yet.) Keep that in mind, okay? :)
> 
> Interesting fun fact: My high school's mascot was the Raider. Weren't terribly scary on the field, but they could totally Math and Science you to death (and then the English teachers would dig up your corpse and beat it with grammar and symbolism.) Imagine a lot of crying; fear of constant failure (anything less than an A- might as well have been failure there - I was, at best, a C student;) and lots of sleep deprivation and you pretty much have my high school years in a nutshell.
> 
> Interesting fun fact #2: I actually don't like baseball, but I know loads of shit about it, thanks to my dad.

It had all started with one ill-fated wager.

As Ichabod sat on his bed with his head in his hands, he mulled over his current predicament and how he'd gotten himself there. It had all started with a little league baseball game he'd attended with Abbie the day before, between the six year old divisions of the Bulldogs vs. the Raiders - the latter of which were apparently based on revolutionary soldiers such as himself. In fact, due to Ichabod's style of clothing, the snaggle-toothed six year olds who took the field that day all thought that he was their mascot - something that had made Abbie snort with laughter (in between her razzing the umpire, of course.) When he'd protested, making a few rather scathing comments about the unsightly way people in this dreadful future dressed, Abbie came up with an idea: a wager on the game they were watching. Each would chose a team, and the loser of the bet would spend a week wearing clothing from the era of the winner (no matter how frustrating and silly they might look.) Ichabod had nodded, shook her hand, and quickly chose the Raiders.

Naturally, the tiny Raiders lost to a freak, broken bat pop fly from a rather surly six year old that just happened to zoom over the left field fence. Ichabod was quite certain it was a foul, and that the umpire had been briefly blinded by the sunlight and had no idea what he was even seeing; however, none of the two-hundred and fifty year old insults that Ichabod had screamed after the call did anything to change the ump's mind - not even the seriously naughty ones in Middle English. Abbie had won, and Ichabod was sentenced to a week of skinny jeans and sneakers.

Of course, the prospect of having his nethers strangled by the tight, unforgiving trousers was one thing. The button-down shirts with the strange, striped patterns were quite another. But there was one horror that he'd not expected: the underwear. Tight trousers meant that only a certain type of modern underwear would do...

"Thong." He muttered to himself, still sitting on the bed, remembering what Abbie had called them. "Thoooong."

He had been certain it was some sort of sling at first, when Abbie had first handed him a pair. "Are we to use this against the Horseman?" He'd asked her. "This design seems inefficient."

Abbie had giggled, before whispering in his ear that they were indeed underwear, and not a weapon. Ichabod turned a bright shade of red, and then eyed the stringy article of clothing with fear and trepidation. 

"These... are part of our wager?" He'd said, "I am to wear these?"  
"Yes." She replied, her cheeks flushing red.  
"And these... go on my..."  
"Yes." Abbie replied. She smirked and turned away.  
"I see." He then said, twisting the scanty underwear around in his fingers and turning more and more red by the moment. "And I take it the animal print is merely a thing of coincidence?"  
"It was the only ones in your size."  
"And how is it that you know my size?"

Abbie's face and ears went as red as a tomato. She opened her mouth to speak, but no sound came out.

"Right." Ichabod responded, smiling sheepishly. He tossed the underwear onto a small pile of modern-day clothing that Abbie had brought, turned, and headed into his bedroom.

"Crane?" Abbie said, before he closed the door. "Be careful with those. You don't want to give yourself a wedgie."

He raised an eyebrow in reply, but closed the door before she could explain to him what a "wedgie" was. He considered "googling" it with his computer; however, after the last time he'd attempted to locate a place that was "hot, wet, deep and smelly" using that search engine, he'd become terribly afraid of what sorts of naughtiness that thing was capable of producing. 

He plodded over to the bed, and plopped down, sitting the skinny jeans and shirt next to him. He picked up the thong and twisted it in his fingers once again. It wasn't too difficult for him to figure out how the scanty, zebra-striped underwear were supposed to go on. With a loud sigh, he inched off his 18th century style trousers and drawers, leaving him bare from the waist down. He stood up, and making sure the thong was situated corrected, he stepped into it and jerked them upwards quickly.

"Hmm." He muttered, inspecting his new britches in the mirror. They weren't the most comfortable things in the world, and they were quite... showy - both in print and in bare skin - but he had experienced far worse things before. "I can manage," he thought to himself.

Ichabod then gave a sigh, and then grabbed onto the pair of skinny jeans. He pulled one leg on, and then the other, and went through the long, dreaded task of trying to pull up the cursed things. He fought for several minutes, tugging and pulling at the unforgiving fabric until he finally had them in place. He then buttoned them, and yanked the zipper upwards, sucking in his middle as much as he could. "This must be what a corset feels like." He mumbled somewhat out of breath, eyeing himself in the mirror.

Shirt and socks were next. He stripped his usual tunic and quickly threw on the strangely striped shirt Abbie had found for him, buttoning it up swiftly. He then went to sit down on the bed to put on the equally strange patterned socks ("are those kittens?" he questioned, noting the pattern;) but he dropped them by accident. So, he bent over... and that's when all hell broke loose.

Ichabod felt a stretch, and then a pull, and then the piddly excuse for underpants he'd put on became wedged between his butt cheeks. He gave a soft groan feeling the sudden discomfort that was plaguing his rear. He attempted to reach his hand into his trousers to tug the thong back into place, but the jeans were so tight they prevented it. Grabbing onto the button in front, he undid it quickly and then attacked the zipper, trying as hard as he could to loosen it; however, the damned thing had become stuck, and refused to budge.

"Uh-oh." He said, still tugging at the zipper in hopes of freeing himself - all to no avail.

He began to hop around, pulling and yanking and trying everything he could to dislodge the thong from his rear. Groaning and grunting all the while, he kicked over a stool, ripped the telephone wires out of the wall, and knocked over and broke a lamp - all in an attempt to free his buttocks from their ungodly torment. He had fought monsters and demons, and he was going to be damned if such a silly thing as underwear was going to be the end of him.

With each hop, however, the thong became more and more twisted up, pulling harshly up his crack and becoming stuck there.

"Crane? You alright?" Abbie called from the other side of the door.  
"ARGH!" He moaned in reply, still trying to excavate the thong from his crack.  
"I'm coming in!" Abbie told him.  
"NOOOO!" He yelled at her.

But, it was too late.

The door flung open, and Abbie stood there, her hand on her sidearm, staring at him in shock. Ichabod had managed to get one hand inside the back of his pants, but it had become lodged there. One leg was up on his bedpost, his other hand was clawing the fabric that encased his extended leg. A bit of zebra-striped fabric stuck out from the waist of his trousers, far, far away from where it normally should've been.

"I appear to have discovered what a 'wedgie' is." He told her, his voice slightly squeaky, as all the color draining out of his face.

***

**FIVE MINUTES LATER...**

"While I'm ever grateful for your assistance, Miss Mills, I..." Ichabod stammered, as he sat on his bed next to Abbie, wearing his usual trousers once again, "...I am very sorry you had to see _that._ "  
"Uh-huh." Abbie replied, staring blankly in front of her with a strange smile on her face.  
"It was quite improper." He said.  
"Uh-huh."  
"I had no idea that those blasted trousers would drag those scanty drawers down with them. I'm aware that they didn't leave much to the imagination as it were, but I had no idea that you would see..."  
"...Everything." Abbie said, grinning from ear to ear.  
"Yes... everything." Ichabod said with a flustered sigh. "It was a shock to us all. Are you sure you're quite alright?"

Abbie chuckled.

"I've never been better." She said, still smiling.


End file.
